By Sharon Oliver
Contributing Writer
BOSTON – Boston born and disgraced FBI agent John Joseph Connolly Jr. crossed the line in his relationship with the late mob boss James “Whitey” Bulger.
Childhood connection
Connolly grew up in the Old Harbor Housing Project in South Boston just a few doors down from the Bulger family and was a childhood friend of Billy, the future state politician and younger brother of notorious mob boss Whitey. Reportedly, a 19-year-old Whitey Bulger, who was already head of the Mercer Street Gang, once chased away bullies looking for a fight with a then-8-year-old Connolly over a ball.
The future FBI agent and his family moved away from the neighborhood when he was 12 years old and while Bulger rose up in the ranks in Boston’s criminal underworld with the Winter Hill Gang, Connolly attended Boston College and began his FBI career in the Baltimore and San Francisco field offices before being transferred to Boston in 1973. Two years later, he would form an illicit alliance with his old neighbor and cross a line that would land him behind bars.
In 1975, Connolly convinced Bulger to become an informant. In exchange for receiving information on rival gang members, Connolly agreed to provide protection for Bulger against prosecution for his illegal activities. This partnership lasted 15 years and allowed Bulger to build a criminal empire which included drugs. It also bolstered Connolly’s career by enabling him to take down crime figures like Gennaro Angiulo, the head of Boston’s Italian Mafia, and the Patriarca crime family of Rhode Island. Thanks to Connolly, prosecutors alleged, Bulger got away with many crimes.
Indicted after retirement
Connolly retired in 1990, but his nefarious deeds came to light in 1998 after it was learned that he tipped off Bulger and his partner Stephen Flemmi, telling them to flee. The former agent was indicted in 1999 on charges of falsifying FBI reports to cover the crimes of Bulger and Flemmi, accepting bribes, racketeering, obstruction of justice and lying to an FBI agent. He was convicted in 2002 and sentenced to 10 years in prison.
Having leaked information which prompted Bulger to take a hit out on a man named John Callahan, Connolly was convicted on state charges of second-degree murder in 2008 and was transferred to a Florida prison in 2011 to serve a 40-year sentence. Callahan allegedly had information that could have implicated Bulger in a murder.
Medical release parole
Connolly asked for permission to serve the remainder of his sentence on home confinement due to fears of contracting COVID-19 in 2020, citing a 2018 federal law allowing for compassionate release under “extraordinary” circumstances, such as age, health and other critical factors. Although a Miami-Dade judge initially declined the request, Connolly was eventually granted a medical release in 2021 with the belief that Connolly was terminally ill with cancer and did not have long to live.
In 2023, a Florida parole board ruled in favor of the 84-year-old Connolly continuing his convalescence in his Massachusetts home with his wife Elizabeth. The interstate compact specifies a “termination of supervision” scheduled for December 2047. However, Connolly has outlived the initial life expectancy, and the parole board may revisit the situation.
Connolly was one of the primary agents involved in developing the Top Echelon Criminal Informants Program in New England and received eight commendations from every director of the FBI up until his retirement, starting with J. Edgar Hoover. U.S. Attorney Michael Sullivan once told The New York Times, “John Connolly became a Winter Hill Gang operative masquerading as an FBI agent.” The relationship between Connolly and Bulger is depicted in the 2015 film “Black Mass.”
RELATED CONTENT:
From Somerville to “The Godfather,” actor Alex Rocco was the real deal
Rocker and art thief Myles Connor’s wild past immortalized in film
